5-(4-(1,2-Dithiolan-3-yl)butyl)-3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazole | 948565-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-(1,2-Dithiolan-3-yl)butyl)-3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazole
• 英文别名: 3-(3,4-dimethoxyphenyl)-5-[4-(dithiolan-3-yl)butyl]-1,2,4-oxadiazole
• CAS: 948565-52-4
• 化学式: C₁₇H₂₂N₂O₃S₂
• 分子量: 366.505
• InChiKey: UTLPSFFHCKTCTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(4-(1,2-Dithiolan-3-yl)butyl)-3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazole 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以95%的产率得到7-[3-(3,4-Dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]heptane-1,3-dithiol
  参考文献：
  名称：

  Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity

  摘要：

  We designed and synthesized new analogues containing 1,2-dithiolane-3-alkyl and protected or free catechol moieties connected through heteroaromatic rings such as triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, tetrazole or thiazole in order to explore the influence of the bioisosteric replacement of the amide group on the neuroprotective activity of the lipoic acid/dopamine conjugate. Evaluation of the activity of the new compounds, using glutamate-challenged hippocampal HT22 cells, showed that incorporation of heteroaromatic rings in the alkyl-1,2-dithiolane moieties in conjunction with another antioxidant, in this case catechol, may result in strong neuroprotective activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.036
• 作为产物：
  描述：

  N'-(5-(1,2-dithiolan-3-yl)pentanoyloxy)-3,4-dimethoxybenzimidamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到5-(4-(1,2-Dithiolan-3-yl)butyl)-3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity

  摘要：

  We designed and synthesized new analogues containing 1,2-dithiolane-3-alkyl and protected or free catechol moieties connected through heteroaromatic rings such as triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, tetrazole or thiazole in order to explore the influence of the bioisosteric replacement of the amide group on the neuroprotective activity of the lipoic acid/dopamine conjugate. Evaluation of the activity of the new compounds, using glutamate-challenged hippocampal HT22 cells, showed that incorporation of heteroaromatic rings in the alkyl-1,2-dithiolane moieties in conjunction with another antioxidant, in this case catechol, may result in strong neuroprotective activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.036